Hydrochloric Acid → 6-Isobutyl-benzo[1,3]dioxole-4-boronic acid

HRID 460308노트

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HRID 460308 반응식
Br[C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[Li]CCCC.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.Cl>C1COCC1.C(OCC)(=O)C>[CH2:11]([C:4]1[CH:3]=[C:2]([B:24]([OH:25])[OH:23])[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1)[CH:12]([CH3:14])[CH3:13]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 184454154-Bromo-6-isobutyl-benzo[1,3]dioxoleHCID 178418339Butyllithium

생성물 1

HCID 184454206-Isobutyl-benzo[1,3]dioxole-4-boronic acid수율 55%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

To a mixture of 4-bromo-6-isobutyl-benzo[1,3]dioxole (232 mg, 0.90 mmol) in THF (3 mL) cooled to −78° C. under an atmosphere of argon was added n-BuLi (0.72 mL, 2.5 M, 1.80 mmol) dropwise. The reaction mixture was stirred for 5 minutes and triisopropylborate (0.62 mL, 2.71 mmol) was added dropwise. The mixture was stirred at −50° C. for 2 hours then warmed up to room temperature and stirred overnight at room temperature. 2.0 N HCl was slowly added to the reaction mixture. After 30 minutes the mixture was diluted with ethyl acetate and the layers separated. The organic layer was further washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (30% ethyl acetate in hexane) to give 110 mg of 6-isobutyl-benzo[1,3]dioxole-4-boronic acid (55%).

후처리

  1. stirringThe mixture was stirred at −50° C. for 2 hours
  2. temperaturethen warmed up to room temperature
  3. stirringstirred overnight at room temperature
  4. customthe layers separated
  5. washThe organic layer was further washed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-6a27939b9ebc432fb5ea79fb295c87df
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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